catena-Poly­[disodium [[tris­(formato-κO)copper(II)]-μ2-formato-κ2O:O′]], with partial substitution of formate by acetate, Na2n[Cu(O2CH)4−x(O2CCH3)x]n (x = 0.28)

Golobič, A.; Klančar, K.; Šegedin, P.

doi:10.1107/S1600536803005567

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catena-Poly[disodium [[tris(formato-κO)copper(II)]-μ₂-formato-κ²O:O′]], with partial substitution of formate by acetate, Na_2n[Cu(O₂CH)_4−x(O₂CCH₃)_x]_n (x = 0.28)

A. Golobič, K. Klančar and P. Šegedin

The structure of the title compound, Na₂[Cu(CHO₂)_3.72(C₂H₃O₂)_0.28], is built of sodium cations and Cu^II complex anions; the latter are linked into infinite chains. The Cu^II atoms are coordinated by five O atoms belonging to five formate ligands, forming a distorted square-pyramidal coordination. Four symmetry-independent formate ligands are bonded to the Cu atom with Cu—O distances in the range 1.9370 (10)–1.9886 (8) Å. The fifth formate ligand, bonded to the Cu^II atom at a longer distance of 2.2889 (9) Å, forms a bridge to the neighbouring copper(II) ion which is symmetry-related to the original ion by a twofold screw axis. Thus, infinite chains are formed along the b axis. One of the terminal formate ligands is disordered; 28.4 (13)% of its sites are occupied by acetate, which was present in the starting material and was not completely displaced in the course of the reaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005567/ya6153sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005567/ya6153Isup2.hkl Contains datablock I

CCDC reference: 209887

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (O-C) = 0.002 Å
R factor = 0.026
wR factor = 0.018
Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_type* data.
          Atom count from _chemical_formula_sum:C4.28 H4.56 Cu1 Na2 O8
          Atom count from the _atom_type data:  C4.25 H4.5 Cu1 Na2 O8

CELLZ_01
         From the CIF: _cell_formula_units_Z    4
         From the CIF: _chemical_formula_sum  C4.28 H4.56 Cu1 Na2 O8
         TEST: Compare cell contents of formula and atom_type data

         atom    Z*formula  atom_type diff
         H         18.24     18.26    0.02
         Cu         4.00      4.00    0.00
         O         32.00     32.00    0.00
         C         17.12     17.13    0.01
         Na         8.00      8.00    0.00
          WARNING: Cell contents from the formula and atom_type data differ!

Comment top

Copper carboxylates are well known to form a variety of structures, even with the ligands of the same homologous series. One of the objectives of our recent work involved the development of new synthetic methods for the preparation of copper formates, both with and without additional N– or O-donor ligands. Recently, we reported the synthesis and the crystal structure of the new orthorhombic form of a polymeric adduct of copper(II) formate–formic acid (1:2) (Lah et al., 2002). We present here the structure of a new ionic compound, catena-Poly[disodium [[tris(formato-κO)copper(II)]-µ₂-formato-κ²O:O']], (I).

The structure of (I) is built of sodium cations and tetraformatocopper(II) complex anions; the latter are linked into infinite chains. The Cu^II atom in the anion is coordinated by five O atoms belonging to five formate ligands and forming a distorted square-pyramidal coordination environment (Fig. 1). Distances between the Cu and Oy1 atoms (where y is 1, 2, 3 and 4 for the first, second, third and fourth symmetry-independent formate ligands, respectively) range from 1.9370 (10) to 1.9886 (8) Å. The fifth ligand, which is symmetry related to the first formate ion by a twofold screw axis, is bonded to the Cu atom via atom O12, at a longer distance of 2.2889 (9) Å, and forms a bridge between two copper(II) ions. The result of such Cu—O11—C1—O12—Cu bridging is infinite chains of connected copper polyhedrons along the b axis (Fig. 2). The torsion angles around the bridging bonds, Cu—O11—C1—O12 and O11—C1—O12—Cuⁱ [symmetry code (i): 1 - x, 1/2 + y, 3/2 - z], of 0.73 (15) and -178.54 (9)°, respectively, show that the mode of formate-bridging is syn–anti (Sletten & Jensen, 1973). The second O atoms of non-bridging formate ligands are coordinated to the sodium cations. The Na1 and Na2 cations are surrounded by five and six formate O atoms, respectively. The Na—O distances are in the range 2.3559 (11)–2.5398 (12) Å.

One of the terminal formate ligands was found to be disordered. The resolution of the disorder and refinement of the disordered model showed that in 28.4 (13)% of the unit cells the formate group failed to displace the acetate ligand of the starting material.

Experimental top

Single crystals of the title compound were prepared by the reaction of copper acetate dihydrate and sodium formate. 1 mmol of Cu₂(C₂H₃O₂)₄·2H₂O and 16 mmol of Na(CHO₂) were refluxed with 30 ml of slightly acidified (using formic acid) methanol for one hour. The undissolved solid residue was filtered off and the resulting solution was left to stand at 278 K for 20 h. Blue crystals obtained from the solution were used for X-ray diffraction.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: Xtal3.6 (Hall et al., 1999); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: Xtal3.6.

Figures top

	Fig. 1. A view of the structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (i) 1 - x, 1/2 + y, 3/2 - z]. Dashed lines depict atoms belonging to the minor component of the disorder.
	Fig. 2. The packing of the title compound, viewed along the a axis.

(I) top

Crystal data top

Na₂[Cu(CHO₂)_3.72(C₂H₃O₂)_0.28]	F(000) = 581.02
M_r = 293.58	D_x = 2.121 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 2160 reflections
a = 7.0867 (4) Å	θ = 1.0–27.5°
b = 9.4514 (4) Å	µ = 2.49 mm⁻¹
c = 13.8277 (8) Å	T = 293 K
β = 96.993 (2)°	Prism, blue
V = 919.28 (8) Å³	0.23 × 0.22 × 0.21 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (DENZO–SMN; Otwinovski & Minor, 1997)	h = −9→9
T_min = 0.564, T_max = 0.593	k = −12→12
12602 measured reflections	l = −17→17
2069 independent reflections

Refinement top

Refinement on F	8 constraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: difference Fourier map
wR(F²) = 0.018	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	REGINA weighting scheme (Wang & Robertson, 1985)
2019 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

Na₂[Cu(CHO₂)_3.72(C₂H₃O₂)_0.28]	V = 919.28 (8) Å³
M_r = 293.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0867 (4) Å	µ = 2.49 mm⁻¹
b = 9.4514 (4) Å	T = 293 K
c = 13.8277 (8) Å	0.23 × 0.22 × 0.21 mm
β = 96.993 (2)°

Data collection top

Nonius KappaCCD diffractometer	2069 independent reflections
Absorption correction: multi-scan (DENZO–SMN; Otwinovski & Minor, 1997)	1947 reflections with I > 2σ(I)
T_min = 0.564, T_max = 0.593	R_int = 0.026
12602 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.018	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	Δρ_max = 0.52 e Å⁻³
2019 reflections	Δρ_min = −0.83 e Å⁻³
156 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu	0.45912 (2)	0.271510 (10)	0.815910 (10)	0.01988 (11)
Na1	0.86246 (6)	0.53549 (5)	0.38067 (4)	0.0287 (2)
Na2	0.36454 (6)	−0.04844 (5)	0.88281 (4)	0.0292 (2)
O11	0.57597 (12)	0.22579 (8)	0.69824 (6)	0.0239 (4)
O12	0.51143 (13)	0.00187 (9)	0.73108 (7)	0.0309 (4)
O21	0.35036 (12)	0.33218 (9)	0.93095 (7)	0.0297 (4)
O22	0.35322 (12)	0.12659 (9)	1.01174 (6)	0.0276 (4)
O31	0.20493 (12)	0.27526 (9)	0.73715 (7)	0.0301 (4)
O32	0.10223 (12)	0.08245 (10)	0.80815 (7)	0.0344 (4)
O41	0.69090 (13)	0.19371 (11)	0.89177 (7)	0.0347 (4)
O42	0.88384 (13)	0.16723 (12)	1.02695 (8)	0.0399 (5)
C1	0.57681 (18)	0.09481 (13)	0.68162 (9)	0.0260 (5)
C2	0.31543 (16)	0.25354 (13)	1.00014 (9)	0.0239 (5)
C3	0.08125 (17)	0.18544 (16)	0.75337 (10)	0.0342 (6)
C4	0.78898 (19)	0.24076 (16)	0.96580 (10)	0.0331 (7)
H1	0.631 (3)	0.070 (2)	0.6313 (19)	0.042 (5)*
H2	0.255 (2)	0.303 (2)	1.0497 (14)	0.032 (4)*
H3	−0.035 (4)	0.201 (2)	0.7202 (18)	0.046 (5)*
C41	0.8518 (8)	0.3942 (6)	0.9528 (4)	0.043 (3)*	.284 (13)
H4	0.767 (4)	0.330 (4)	0.979 (2)	0.043 (3)*	.716 (13)
H41	0.93368	0.39690	0.89758	0.043 (3)*	.284 (13)
H42	0.74138	0.45572	0.93813	0.043 (3)*	.284 (13)
H43	0.93446	0.43249	1.01245	0.043 (3)*	.284 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.02128 (11)	0.01892 (11)	0.01975 (11)	0.00162 (4)	0.00371 (6)	0.00246 (4)
Na1	0.0288 (2)	0.0280 (2)	0.0308 (3)	0.00217 (17)	0.00996 (18)	−0.00075 (18)
Na2	0.0306 (2)	0.0261 (2)	0.0311 (3)	−0.00397 (17)	0.00460 (18)	0.00033 (18)
O11	0.0294 (4)	0.0184 (4)	0.0247 (4)	0.0006 (3)	0.0067 (3)	0.0019 (3)
O12	0.0419 (4)	0.0186 (4)	0.0351 (5)	0.0003 (3)	0.0166 (4)	−0.0003 (4)
O21	0.0383 (4)	0.0257 (4)	0.0268 (4)	0.0026 (3)	0.0107 (3)	0.0033 (4)
O22	0.0326 (4)	0.0256 (5)	0.0249 (4)	0.0009 (3)	0.0038 (3)	−0.0030 (3)
O31	0.0231 (4)	0.0361 (5)	0.0307 (5)	−0.0018 (3)	0.0019 (3)	0.0111 (4)
O32	0.0295 (4)	0.0365 (5)	0.0376 (5)	0.0027 (3)	0.0056 (4)	−0.0107 (4)
O41	0.0338 (5)	0.0378 (5)	0.0306 (5)	0.0108 (4)	−0.0035 (4)	−0.0024 (4)
O42	0.0329 (4)	0.0509 (6)	0.0342 (5)	−0.0011 (4)	−0.0034 (4)	−0.0117 (4)
C1	0.0346 (5)	0.0204 (6)	0.0246 (6)	0.0033 (5)	0.0105 (5)	−0.0007 (5)
C2	0.0248 (5)	0.0279 (6)	0.0197 (6)	0.0002 (4)	0.0048 (4)	−0.0008 (5)
C3	0.0200 (6)	0.0460 (7)	0.0357 (7)	−0.0045 (5)	−0.0012 (5)	0.0142 (6)
C4	0.0367 (7)	0.0307 (8)	0.0305 (7)	0.0053 (5)	−0.0017 (6)	0.0021 (6)

Geometric parameters (Å, º) top

Cu—O11	1.9616 (9)	O11—C1	1.2592 (14)
Cu—O21	1.9370 (10)	O12—C1	1.2374 (16)
Cu—O31	1.9886 (8)	O21—C2	1.2597 (16)
Cu—O41	1.9798 (9)	O22—C2	1.2356 (15)
Cu—O12	2.2889 (9)	O31—C3	1.2598 (16)
Na1—O22	2.4176 (10)	O32—C3	1.2312 (17)
Na1—O42	2.4198 (11)	O41—C4	1.2472 (16)
Na1—O31	2.4274 (10)	O42—C4	1.2294 (17)
Na1—Na2	3.5345 (6)	C1—H1	0.87 (3)
Na1—O41	2.4980 (11)	C2—H2	0.97 (2)
Na1—O32	2.3559 (11)	C3—H3	0.91 (2)
Na2—O12	2.4987 (11)	C4—C41	1.534 (6)
Na2—O22	2.4406 (10)	C4—H4	0.88 (4)
Na2—O32	2.3631 (10)	C41—H4	0.95 (3)
Na2—O11	2.4702 (9)	C41—H41	1.014
Na2—O22	2.4417 (9)	C41—H42	0.976
Na2—O42	2.5398 (12)	C41—H43	1.019

O11—Cu—O21	175.40 (4)	C1—O11—Na2	139.60 (8)
O11—Cu—O31	89.74 (4)	Na2—O12—C1	145.23 (8)
O11—Cu—O41	87.18 (4)	Na2—O12—Cu	96.84 (3)
O11—Cu—O12	84.94 (3)	C1—O12—Cu	117.72 (9)
O21—Cu—O31	91.15 (4)	Cu—O21—C2	125.71 (8)
O21—Cu—O41	93.57 (4)	Na2—O22—C2	126.11 (8)
O21—Cu—O12	90.61 (4)	Na2—O22—Na1	106.71 (4)
O31—Cu—O41	159.16 (4)	Na2—O22—Na2	97.69 (3)
O31—Cu—O12	86.30 (3)	C2—O22—Na1	106.41 (8)
O41—Cu—O12	113.91 (4)	C2—O22—Na2	121.34 (7)
O22—Na1—O42	88.66 (4)	Na1—O22—Na2	93.33 (3)
O22—Na1—O31	93.62 (3)	Cu—O31—C3	119.60 (8)
O22—Na1—Na2	43.60 (2)	Cu—O31—Na1	118.15 (4)
O22—Na1—O41	85.53 (3)	C3—O31—Na1	122.12 (8)
O22—Na1—O32	166.72 (4)	Na2—O32—C3	135.42 (8)
O42—Na1—O31	92.75 (4)	Na2—O32—Na1	97.82 (4)
O42—Na1—Na2	131.00 (3)	C3—O32—Na1	126.63 (8)
O42—Na1—O41	138.56 (4)	Cu—O41—C4	130.24 (10)
O42—Na1—O32	86.57 (4)	Cu—O41—Na1ⁱ	131.93 (5)
O31—Na1—Na2	82.25 (2)	C4—O41—Na1ⁱ	97.63 (8)
O31—Na1—O41	128.52 (3)	C4—O42—Na1	164.34 (10)
O31—Na1—O32	98.98 (4)	C4—O42—Na2	103.54 (9)
Na2—Na1—O41	62.33 (2)	Na1—O42—Na2	91.60 (4)
Na2—Na1—O32	142.42 (3)	O11—C1—O12	125.92 (12)
O41—Na1—O32	89.86 (4)	O11—C1—H1	115.2 (15)
O12—Na2—O22	122.58 (3)	O12—C1—H1	118.9 (15)
O12—Na2—O32	85.38 (4)	O21—C2—O22	127.74 (12)
O12—Na2—O11	70.84 (3)	O21—C2—H2	113.5 (11)
O12—Na2—O22	99.46 (3)	O22—C2—H2	118.7 (11)
O12—Na2—O42	151.78 (4)	O31—C3—O32	127.43 (11)
O12—Na2—Na1ⁱ	57.86 (2)	O31—C3—H3	114.1 (14)
O22—Na2—O32	82.54 (3)	O32—C3—H3	118.5 (14)
O22—Na2—O11	159.98 (4)	O41—C4—O42	124.50 (14)
O22—Na2—O22	82.31 (3)	O41—C4—C41	112.4 (2)
O22—Na2—O42	81.63 (4)	O41—C4—H4	114.6 (18)
O22—Na2—Na1ⁱ	95.99 (3)	O42—C4—C41	118.2 (2)
O32—Na2—O11	115.00 (4)	O42—C4—H4	119.7 (19)
O32—Na2—O22	164.33 (4)	C4—C41—H41	108.3 (4)
O32—Na2—O42	83.72 (4)	C4—C41—H42	110.6 (4)
O32—Na2—Na1ⁱ	135.34 (3)	C4—C41—H43	112.8 (4)
O11—Na2—O22	80.62 (3)	H4—C41—H41	138 (2)
O11—Na2—O42	90.45 (4)	H4—C41—H42	86 (2)
O11—Na2—Na1ⁱ	78.49 (2)	H4—C41—H43	104.2 (19)
O22—Na2—O42	98.00 (4)	H41—C41—H42	110.3 (5)
O22—Na2—Na1ⁱ	43.07 (2)	H41—C41—H43	106.0 (5)
O42—Na2—Na1ⁱ	140.51 (3)	H42—C41—H43	108.9 (5)
Cu—O11—C1	112.32 (8)	C4—H4—C41	113 (3)
Cu—O11—Na2	107.38 (4)

O11—Cu—Na2—O12	−2.04 (3)	O22—Na2—O22—Na2	−0.00 (3)
O11—Cu—Na2—O22	163.63 (3)	O22—Na2—O22—Na1ⁱ	−107.37 (3)
O11—Cu—Na2—O32	−103.52 (4)	O32—Na2—O22—Na2	14.94 (16)
O11—Cu—Na2—O11	−0.91 (4)	O32—Na2—O22—Na1ⁱ	−92.43 (15)
O11—Cu—Na2—O22	89.38 (4)	O11—Na2—O22—Na2	−169.49 (4)
O11—Cu—Na2—O42	−150.07 (5)	O11—Na2—O22—Na1ⁱ	83.14 (3)
O11—Cu—Na2—Na1ⁱ	59.67 (3)	O42—Na2—O22—Na2	−80.36 (4)
O21—Cu—Na2—O12	178.69 (3)	O42—Na2—O22—Na1ⁱ	172.27 (4)
O21—Cu—Na2—O22	−15.64 (3)	Na1ⁱ—Na2—O22—Na2	107.37 (4)
O21—Cu—Na2—O32	77.22 (4)	Na1ⁱ—Na2—O22—Na1ⁱ	−0.000 (19)
O21—Cu—Na2—O11	179.82 (4)	Cu—Na2—O42—Na1	45.10 (6)
O21—Cu—Na2—O22	−89.89 (4)	O12—Na2—O42—Na1	−64.01 (9)
O21—Cu—Na2—O42	30.66 (5)	O22—Na2—O42—Na1	87.25 (4)
O21—Cu—Na2—Na1ⁱ	−119.60 (3)	O32—Na2—O42—Na1	3.90 (4)
O31—Cu—Na2—O12	87.41 (4)	O11—Na2—O42—Na1	−111.21 (4)
O31—Cu—Na2—O22	−106.92 (4)	O22—Na2—O42—Na1	168.20 (4)
O31—Cu—Na2—O32	−14.07 (4)	Na1ⁱ—Na2—O42—Na1	176.51 (3)
O31—Cu—Na2—O11	88.54 (4)	Cu—Na2—Na1ⁱ—O41	20.61 (3)
O31—Cu—Na2—O22	178.83 (4)	Cu—Na2—Na1ⁱ—O22	135.64 (3)
O31—Cu—Na2—O42	−60.62 (5)	O12—Na2—Na1ⁱ—O41	81.96 (4)
O31—Cu—Na2—Na1ⁱ	149.11 (3)	O12—Na2—Na1ⁱ—O22	−163.01 (4)
O41—Cu—Na2—O12	−86.14 (4)	O22—Na2—Na1ⁱ—O41	−43.04 (4)
O41—Cu—Na2—O22	79.53 (4)	O22—Na2—Na1ⁱ—O22	71.99 (4)
O41—Cu—Na2—O32	172.38 (4)	O32—Na2—Na1ⁱ—O41	42.40 (5)
O41—Cu—Na2—O11	−85.01 (4)	O32—Na2—Na1ⁱ—O22	157.43 (6)
O41—Cu—Na2—O22	5.28 (4)	O11—Na2—Na1ⁱ—O41	156.45 (4)
O41—Cu—Na2—O42	125.82 (5)	O11—Na2—Na1ⁱ—O22	−88.53 (4)
O41—Cu—Na2—Na1ⁱ	−24.44 (3)	O22—Na2—Na1ⁱ—O41	−115.03 (4)
O12—Cu—Na2—O12	121.7 (2)	O22—Na2—Na1ⁱ—O22	0.00 (4)
O12—Cu—Na2—O22	−72.6 (2)	O42—Na2—Na1ⁱ—O41	−127.12 (6)
O12—Cu—Na2—O32	20.3 (2)	O42—Na2—Na1ⁱ—O22	−12.10 (6)
O12—Cu—Na2—O11	122.9 (2)	Cu—O11—C1—O12	0.73 (15)
O12—Cu—Na2—O22	−146.8 (2)	Cu—O11—C1—H1	−178.0 (15)
O12—Cu—Na2—O42	−26.3 (2)	Na2—O11—C1—O12	−167.94 (8)
O12—Cu—Na2—Na1ⁱ	−176.6 (2)	Na2—O11—C1—H1	13.4 (16)
Na2—Cu—O11—C1	1.61 (8)	Cu—O11—Na2—O12	0.45 (3)
Na2—Cu—O11—Na2	173.95 (3)	Cu—O11—Na2—O22	−134.92 (9)
O21—Cu—O11—Na2	−15.2 (4)	Cu—O11—Na2—Na1	−59.28 (3)
O31—Cu—O11—C1	−86.49 (8)	C1—O11—Na2—O12	169.47 (12)
O31—Cu—O11—Na2	85.84 (4)	C1—O11—Na2—O22	34.10 (18)
O41—Cu—O11—C1	72.89 (8)	C1—O11—Na2—Na1	109.74 (12)
O41—Cu—O11—Na2	−114.78 (4)	Na2—O12—C1—O11	−5.4 (2)
O12—Cu—O11—C1	−172.80 (8)	Na2—O12—C1—H1	173.2 (16)
O12—Cu—O11—Na2	−0.47 (3)	Cu—O12—C1—O11	−178.54 (9)
Na2—Cu—O21—C2	13.73 (9)	Cu—O12—C1—H1	0.1 (16)
O31—Cu—O21—C2	101.81 (9)	Na2—O12—Cu—O11	0.44 (3)
O41—Cu—O21—C2	−57.88 (9)	C1—O12—Cu—O11	176.49 (9)
O12—Cu—O21—C2	−171.88 (9)	Cu—O21—C2—O22	4.88 (17)
Na2—Cu—O31—C3	16.69 (10)	Cu—O21—C2—H2	−177.1 (11)
Na2—Cu—O31—Na1	−167.29 (5)	Na2—O22—C2—O21	−31.88 (17)
O11—Cu—O31—C3	115.52 (11)	Na2—O22—C2—H2	150.2 (11)
O11—Cu—O31—Na1	−68.46 (5)	Na1—O22—C2—H2	24.3 (11)
O21—Cu—O31—C3	−68.99 (11)	Na2—O22—C2—O21	97.77 (13)
O21—Cu—O31—Na1	107.03 (5)	Na2—O22—C2—H2	−80.2 (11)
O41—Cu—O31—C3	34.16 (18)	Na2—O22—Na1—Na2	99.06 (4)
O41—Cu—O31—Na1	−149.82 (10)	C2—O22—Na1—Na2	−124.07 (8)
O12—Cu—O31—C3	−159.53 (11)	Na2—O22—Na1—Na2	−0.000 (17)
O12—Cu—O31—Na1	16.49 (5)	Na2—O22—Na2—O42	80.36 (4)
Na2—Cu—O41—C4	−124.50 (12)	Na2—O22—Na2—Na1	−107.37 (4)
Na2—Cu—O41—Na1ⁱ	49.15 (5)	Na2—O22—Na2—O22	0.00 (3)
O11—Cu—O41—C4	135.28 (12)	C2—O22—Na2—O42	−60.75 (10)
O11—Cu—O41—Na1ⁱ	−51.07 (6)	C2—O22—Na2—Na1	111.51 (10)
O21—Cu—O41—C4	−40.18 (12)	C2—O22—Na2—O22	−141.12 (10)
O21—Cu—O41—Na1ⁱ	133.47 (6)	Na1—O22—Na2—O42	−172.27 (4)
O31—Cu—O41—C4	−142.90 (13)	Na1—O22—Na2—Na1	0.000 (17)
O31—Cu—O41—Na1ⁱ	30.76 (16)	Na1—O22—Na2—O22	107.37 (3)
O12—Cu—O41—C4	52.08 (13)	Cu—O31—C3—O32	−7.4 (2)
O12—Cu—O41—Na1ⁱ	−134.27 (6)	Cu—O31—C3—H3	172.3 (17)
Na2—Cu—O12—Na2	−124.0 (2)	Na1—O31—C3—O32	176.73 (12)
O11—Cu—O12—Na2	0.44 (3)	Na1—O31—C3—H3	−3.6 (17)
O21—Cu—O12—Na2	179.27 (3)	Cu—O31—Na1—Na2	28.04 (4)
O31—Cu—O12—Na2	−89.62 (4)	C3—O31—Na1—Na2	−156.04 (11)
O41—Cu—O12—Na2	85.09 (4)	Na2—O32—C3—O31	−18.1 (2)
O42—Na1—O22—Na2	−93.49 (4)	Na2—O32—C3—H3	162.2 (17)
O42—Na1—O22—Na2	167.46 (4)	Na1—O32—C3—O31	156.74 (12)
O31—Na1—O22—Na2	173.84 (3)	Na1—O32—C3—H3	−23.0 (18)
O31—Na1—O22—Na2	74.78 (3)	Na2—O32—Na1—O42	4.22 (4)
Na2—Na1—O22—Na2	99.06 (4)	C3—O32—Na1—O42	−172.16 (12)
Na2—Na1—O22—Na2	−0.000 (16)	Cu—O41—C4—O42	152.38 (11)
O41—Na1—O22—Na2	45.45 (4)	Cu—O41—C4—C41	−52.9 (3)
O41—Na1—O22—Na2	−53.61 (3)	Cu—O41—C4—H4	−15 (2)
O32—Na1—O22—Na2	−24.56 (17)	Na1ⁱ—O41—C4—O42	−22.86 (16)
O32—Na1—O22—Na2	−123.62 (15)	Na1ⁱ—O41—C4—C41	131.9 (2)
O22—Na1—Na2—O22	0.00 (4)	Na1ⁱ—O41—C4—H4	170 (2)
O42—Na1—Na2—O22	−16.72 (5)	Cu—O41—Na1ⁱ—Na2	−48.44 (6)
O31—Na1—Na2—O22	−103.61 (4)	Cu—O41—Na1ⁱ—O22	−87.25 (7)
O41—Na1—Na2—O22	115.03 (4)	C4—O41—Na1ⁱ—Na2	126.68 (9)
O32—Na1—Na2—O22	161.72 (6)	C4—O41—Na1ⁱ—O22	87.86 (8)
Cu—Na2—O12—C1	4.84 (13)	Na1—O42—C4—O41	92.2 (4)
Cu—Na2—O12—Cu	178.69 (4)	Na1—O42—C4—C41	−61.2 (5)
O22—Na2—O12—C1	−10.81 (15)	Na1—O42—C4—H4	−101 (2)
O22—Na2—O12—Cu	163.04 (3)	Na2—O42—C4—O41	−72.77 (15)
O32—Na2—O12—C1	67.29 (14)	Na2—O42—C4—C41	133.8 (3)
O32—Na2—O12—Cu	−118.85 (4)	Na2—O42—C4—H4	94 (2)
O11—Na2—O12—C1	−174.22 (15)	C4—O42—Na2—O22	7.78 (10)
O11—Na2—O12—Cu	−0.37 (3)	C4—O42—Na2—Na1	−0.53 (12)
O22—Na2—O12—C1	−97.69 (14)	C4—O42—Na2—O22	88.73 (9)
O22—Na2—O12—Cu	76.17 (3)	Na1—O42—Na2—O22	−168.20 (3)
O42—Na2—O12—C1	134.81 (14)	Na1—O42—Na2—Na1	−176.51 (3)
O42—Na2—O12—Cu	−51.33 (9)	Na1—O42—Na2—O22	−87.25 (4)
Na1ⁱ—Na2—O12—C1	−86.02 (14)	O41—C4—C41—H4	101 (3)
Na1ⁱ—Na2—O12—Cu	87.84 (3)	O41—C4—C41—H41	−61.8 (4)
Cu—Na2—O22—C2	27.73 (9)	O41—C4—C41—H42	59.1 (5)
Cu—Na2—O22—Na1	153.47 (3)	O41—C4—C41—H43	−178.7 (4)
Cu—Na2—O22—Na2	−110.69 (3)	O42—C4—C41—H4	−102 (3)
O12—Na2—O22—C2	42.08 (10)	O42—C4—C41—H41	94.7 (4)
O12—Na2—O22—Na1	167.82 (3)	O42—C4—C41—H42	−144.4 (3)
O12—Na2—O22—Na2	−96.34 (4)	O42—C4—C41—H43	−22.2 (6)
O32—Na2—O22—C2	−37.55 (10)	H4—C4—C41—H4	0 (5)
O32—Na2—O22—Na1	88.19 (4)	H4—C4—C41—H41	−163 (3)
O32—Na2—O22—Na2	−175.97 (4)	H4—C4—C41—H42	−42 (3)
O11—Na2—O22—C2	170.12 (10)	H4—C4—C41—H43	80 (3)
O11—Na2—O22—Na1	−64.14 (11)	O41—C4—H4—C41	−94 (3)
O11—Na2—O22—Na2	31.70 (12)	O42—C4—H4—C41	98 (3)
O22—Na2—O22—C2	138.42 (10)	C41—C4—H4—C41	0.0 (5)
O22—Na2—O22—Na1	−95.84 (4)	C4—C41—H4—C4	−0.00 (13)
O22—Na2—O22—Na2	0.00 (3)	H41—C41—H4—C4	25 (5)
O42—Na2—O22—C2	−122.26 (10)	H42—C41—H4—C4	141 (3)
O42—Na2—O22—Na1	3.48 (4)	H43—C41—H4—C4	−110 (3)
O42—Na2—O22—Na2	99.31 (4)	O12—Cu—O11—Na2	−0.47 (3)
Na1ⁱ—Na2—O22—C2	97.48 (9)	O22—Na1—Na2—O22	−0.00 (4)
Na1ⁱ—Na2—O22—Na1	−136.78 (3)	O22—Na1—Na2—O42	12.10 (6)
Na1ⁱ—Na2—O22—Na2	−40.94 (3)	O22—Na1—Na2—O22	−71.99 (4)
Cu—Na2—O32—C3	21.81 (13)	O11—Na2—O12—Cu	−0.37 (3)
Cu—Na2—O32—Na1	−154.05 (4)	O22—Na2—O12—Cu	163.04 (3)
O12—Na2—O32—C3	−34.26 (14)	Na1—Na2—O12—Cu	87.84 (3)
O12—Na2—O32—Na1	149.89 (4)	O11—Na2—O22—Na1	−64.14 (11)
O22—Na2—O32—C3	89.48 (14)	O11—Na2—O22—Na2	31.70 (12)
O22—Na2—O32—Na1	−86.37 (4)	O12—Na2—O22—Na1	167.82 (3)
O11—Na2—O32—C3	−100.62 (14)	O12—Na2—O22—Na2	−96.34 (4)
O11—Na2—O32—Na1	83.52 (5)	Na1—Na2—O22—Na1	−136.78 (3)
O22—Na2—O32—C3	74.6 (2)	Na1—Na2—O22—Na2	−40.94 (3)
O22—Na2—O32—Na1	−101.31 (15)	O11—Na2—Na1—O31	15.08 (3)
O42—Na2—O32—C3	171.82 (14)	O12—Na2—Na1—O31	−59.40 (4)
O42—Na2—O32—Na1	−4.04 (4)	O22—Na2—Na1—O31	175.60 (3)
Na1ⁱ—Na2—O32—C3	−1.50 (16)	Na1—O22—Na2—Na1	−0.000 (16)
Na1ⁱ—Na2—O32—Na1	−177.36 (3)	Na2—O22—Na2—Na1	−107.37 (4)
Cu—Na2—O11—Cu	−0.56 (5)	O22—Na2—O22—Na2	0.00 (3)
O12—Na2—O11—Cu	0.45 (3)	O22—Na2—O22—Na1ⁱ	95.84 (4)
O22—Na2—O11—Cu	−134.92 (9)	O42—Na2—O22—Na2	−99.31 (4)
O32—Na2—O11—Cu	75.62 (5)	O42—Na2—O22—Na1ⁱ	−3.48 (4)
O22—Na2—O11—Cu	−103.06 (4)	Na1—Na2—O22—Na2	40.94 (3)
O42—Na2—O11—Cu	158.90 (4)	Na1—Na2—O22—Na1ⁱ	136.78 (3)
Na1ⁱ—Na2—O11—Cu	−59.28 (3)	Na2—O22—Na1ⁱ—Na2	−0.000 (16)
Cu—Na2—O22—Na2	63.11 (3)	Na2—O22—Na1ⁱ—O41	53.61 (3)
Cu—Na2—O22—Na1ⁱ	−44.26 (3)	Na2—O22—Na1ⁱ—Na2	−99.06 (4)
O12—Na2—O22—Na2	121.90 (3)	Na2—O22—Na1ⁱ—O41	−45.45 (4)
O12—Na2—O22—Na1ⁱ	14.53 (4)	Na2—O42—Na1—O32	−3.89 (4)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	Na₂[Cu(CHO₂)_3.72(C₂H₃O₂)_0.28]
M_r	293.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.0867 (4), 9.4514 (4), 13.8277 (8)
β (°)	96.993 (2)
V (Å³)	919.28 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.49
Crystal size (mm)	0.23 × 0.22 × 0.21

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO–SMN; Otwinovski & Minor, 1997)
T_min, T_max	0.564, 0.593
No. of measured, independent and observed [I > 2σ(I)] reflections	12602, 2069, 1947
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.018, 1.26
No. of reflections	2019
No. of parameters	156
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.83

Computer programs: COLLECT (Nonius, 2000), DENZO–SMN (Otwinowski & Minor, 1997), DENZO–SMN, SIR97 (Altomare et al., 1999), Xtal3.6 (Hall et al., 1999), ORTEP-3 (Farrugia, 1997), Xtal3.6.

Selected geometric parameters (Å, º) top

Cu—O11	1.9616 (9)	Na2—O11	2.4702 (9)
Cu—O21	1.9370 (10)	Na2—O22	2.4417 (9)
Cu—O31	1.9886 (8)	Na2—O42	2.5398 (12)
Cu—O41	1.9798 (9)	O11—C1	1.2592 (14)
Cu—O12	2.2889 (9)	O12—C1	1.2374 (16)
Na1—O22	2.4176 (10)	O21—C2	1.2597 (16)
Na1—O42	2.4198 (11)	O22—C2	1.2356 (15)
Na1—O31	2.4274 (10)	O31—C3	1.2598 (16)
Na1—O41	2.4980 (11)	O32—C3	1.2312 (17)
Na1—O32	2.3559 (11)	O41—C4	1.2472 (16)
Na2—O12	2.4987 (11)	O42—C4	1.2294 (17)
Na2—O22	2.4406 (10)	C4—C41	1.534 (6)
Na2—O32	2.3631 (10)

O11—Cu—O21	175.40 (4)	O41—Cu—O12	113.91 (4)
O11—Cu—O31	89.74 (4)	O11—C1—O12	125.92 (12)
O11—Cu—O41	87.18 (4)	O21—C2—O22	127.74 (12)
O11—Cu—O12	84.94 (3)	O31—C3—O32	127.43 (11)
O21—Cu—O31	91.15 (4)	O41—C4—O42	124.50 (14)
O21—Cu—O41	93.57 (4)	O41—C4—C41	112.4 (2)
O21—Cu—O12	90.61 (4)	O41—C4—H4	114.6 (18)
O31—Cu—O41	159.16 (4)	O42—C4—C41	118.2 (2)
O31—Cu—O12	86.30 (3)	O42—C4—H4	119.7 (19)

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